CN115161112A - Processing method of squeezed citrus essential oil - Google Patents
Processing method of squeezed citrus essential oil Download PDFInfo
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- CN115161112A CN115161112A CN202210527330.0A CN202210527330A CN115161112A CN 115161112 A CN115161112 A CN 115161112A CN 202210527330 A CN202210527330 A CN 202210527330A CN 115161112 A CN115161112 A CN 115161112A
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- essential oil
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/025—Recovery by solvent extraction
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/022—Refining
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- Organic Chemistry (AREA)
- Edible Oils And Fats (AREA)
Abstract
The invention discloses a method for treating pressed citrus essential oil, which comprises the following steps: mixing and stirring the squeezed citrus essential oil and an extracting agent, freezing and standing to separate the citrus essential oil into layers, and separating out upper-layer essential oil to obtain treated citrus essential oil; wherein the extracting agent is an organic acid solution with the pH value less than or equal to 2. According to the invention, the organic acid solution with the pH value less than or equal to 2 is used as the extracting agent to treat the pressed citrus essential oil, so that the residual pesticide in the essential oil can be removed to the utmost extent without losing the fragrance, and the food safety of the pressed citrus essential oil product is improved.
Description
Technical Field
The invention relates to the technical field of citrus essential oil, and particularly relates to a method for treating squeezed citrus essential oil.
Background
The citrus essential oil has fresh, natural and pleasant citrus fragrance, and is widely applied to flavor blending in the food industry, such as beverages, cakes and ice cream products. The citrus essential oil has various varieties, mainly including sweet oranges, tangerines, lemons, grapefruit and the like, and is popular among consumers.
The squeezing method comprises the steps of puncturing citrus peel oil cells at room temperature or low temperature to enable essential oil to seep out, so that volatile components in citrus can be retained to the maximum extent, the aroma is pure and true, and the reduction degree is high. However, the squeezing method may dissolve the residual pesticide in the essential oil during the production process. Pyrimethanil is a novel fungicide of anilinopyrimidine and can prevent and control botrytis cinerea which has drug resistance on vegetables and fruits to common non-anilinopyrimidine fungicides. Mouse experiments show that the pyrimethanil belongs to weak-allergenic and mild-accumulation pesticides, the pyrimethanil can cause the weight of the liver to be increased, tissue lesion and short-term thyroid poisoning phenomena are caused, and the pyrimethanil can remain in soil for half a year to one year, so that the citrus essential oil prepared by a squeezing method has certain risks to human health.
Disclosure of Invention
The invention mainly aims to provide a method for treating pressed citrus essential oil, which aims to reduce pesticide residues in the pressed citrus essential oil and improve the food safety of products.
In order to achieve the purpose, the invention provides a method for treating pressed citrus essential oil, which comprises the following steps:
mixing and stirring squeezed citrus essential oil and an extracting agent, freezing and standing for layering, and separating out upper-layer essential oil to obtain treated citrus essential oil;
wherein the extracting agent is an organic acid solution with the pH value less than or equal to 2.
Optionally, the organic acid comprises at least one of citric acid, tartaric acid, malic acid, and oxalic acid.
Optionally, the mass ratio of the pressed citrus essential oil to the extracting agent is 1:1-1:2.
Optionally, the stirring time for stirring is 30-60 min.
Optionally, the freezing temperature of the freezing is-20 to 0 ℃, and the freezing time is 12 to 24 hours.
Optionally, the pressed citrus essential oil comprises at least one of sweet orange oil, lemon oil, grapefruit oil, bergamot oil, bitter orange oil, tangerine oil, and kumquat oil.
According to the technical scheme provided by the invention, the pressed citrus essential oil is treated by using an organic acid solution with the pH value of less than or equal to 2 as an extracting agent, so that residual pesticides in the essential oil can be removed to the utmost extent without losing fragrance, and the food safety of the pressed citrus essential oil product is improved.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other related drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a graph of GC-MS analysis results before and after treatment of the press Jin Jieyou in example 1 of the present invention. The implementation, functional features and advantages of the present invention will be further described with reference to the accompanying drawings.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are conventional products which are not indicated by manufacturers and are commercially available. In addition, the meaning of "and/or" appearing throughout includes three juxtapositions, exemplified by "A and/or B" including either A or B or both A and B. In addition, technical solutions between various embodiments may be combined with each other, but must be realized by a person skilled in the art, and when the technical solutions are contradictory or cannot be realized, such a combination should not be considered to exist, and is not within the protection scope of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a method for treating pressed citrus essential oil, which uses organic acid with stronger acidity to treat the pressed citrus essential oil, thereby reducing pesticide residue in the pressed citrus essential oil. In an embodiment of the method for processing pressed citrus essential oil provided by the present invention, the method for processing pressed citrus essential oil comprises the following steps: mixing and stirring the squeezed citrus essential oil and an extracting agent, freezing and standing to separate the citrus essential oil into layers, and separating out upper-layer essential oil to obtain treated citrus essential oil; wherein the extracting agent is an organic acid solution with the pH value less than or equal to 2.
The squeezing method can retain volatile components in the citrus to the maximum extent, has pure fragrance and high reduction degree, but the squeezing method can dissolve residual pesticides in the fruit in the essential oil in the production process, so that certain food safety risk exists in the citrus essential oil in the squeezing method; meanwhile, the citrus essential oil contains more flavonoids, including flavones, flavonols, flavanones and polymethoxylated flavonoids, and the flavonoids have large molecular weight and low polarity, are difficult to dissolve in a water phase system, have poor solubility in flavor blending, are easy to separate out of products, and influence the stability of the products.
According to the technical scheme provided by the invention, the pressed citrus essential oil is treated by using an organic acid solution with the pH value of less than or equal to 2 as an extracting agent, under the environment with the pH value of less than or equal to 2, pyrimethanil is unstable and is easy to degrade, the solubility of flavonoids in an acid solution is improved, flavor components in the citrus essential oil are nonpolar components and are insoluble in water, and simultaneously, the sedimentation of other components with larger polarity can be accelerated under the low-temperature condition.
The organic acid refers to organic compounds with acidity, and organic acids commonly used in the art can be selected, and in some embodiments provided by the present invention, the organic acid includes at least one of citric acid, tartaric acid, malic acid, and oxalic acid, and may be any one of the above organic acids, or a combination of two or more of them, and the mixing ratio thereof is not limited, and all of them fall within the protection scope of the present invention. The organic acids belong to fruit organic acids, are main flavor nutrient substances in fruits, can realize effective extraction treatment of pressed citrus essential oil, and can play a role in increasing the fragrance of the citrus essential oil and enriching the product functionality to a certain extent.
The adding proportion of the pressed citrus essential oil and the extracting agent is not limited, and the pressed citrus essential oil and the extracting agent can be added according to the standard of a conventional extraction method, and specifically, in some embodiments of the treatment method of the pressed citrus essential oil provided by the invention, the mass ratio of the pressed citrus essential oil to the extracting agent is 1:1-1:2. Within the proportion range, the pesticide residue in the pressed citrus essential oil can be effectively degraded, and the flavonoid compounds and other components can be extracted.
The main effect of the stirring and mixing is to mix the citrus fruit essential oil and the extractant, the specific stirring mode is not limited, the common modes of mechanical stirring, magnetic stirring and the like can be adopted, and the stirring speed is not limited, and in some embodiments of the invention, the citrus fruit essential oil and the organic acid solution can be fully and uniformly mixed as long as the stirring time is 30-60 min.
The purpose of the freezing standing is to accelerate the sedimentation of the more polar components in the essential oil, and in some embodiments provided by the invention, the specific parameter conditions of the freezing standing are set as follows: the freezing temperature is-20 to 0 ℃, and the freezing time is 12 to 24 hours. Under the freezing condition, the components with higher polarity in the pressed citrus essential oil can be fully settled, and effective separation of flavonoid compounds and other components is realized.
The method for treating the pressed citrus essential oil provided by the invention is generally applicable to all citrus essential oils produced by pressing, including but not limited to at least one of sweet orange oil, lemon oil, grapefruit oil, bergamot oil, orange oil and kumquat oil, that is, the method provided by the invention can be used for treating any one of sweet orange oil, lemon oil, grapefruit oil, bergamot oil, bitter orange oil, orange oil and kumquat oil produced by pressing, and can also be used for treating mixed essential oil formed by mixing any two or more than two of the citrus essential oils in any proportion, so that residual pesticides in the essential oil can be effectively removed, the content of flavonoid compounds is reduced, and the product stability of the essential oil is improved, and the method belongs to the protection range of the invention.
The technical solutions of the present invention are further described in detail below with reference to specific examples and drawings, it should be understood that the following examples are merely illustrative of the present invention and are not intended to limit the present invention.
Example 1
Mixing and stirring Jin Jieyou and 60wt% citric acid aqueous solution 3242 in a mass ratio of 1:1 for 60min, refrigerating at-20 deg.C for 24h for layering, and separating upper layer essential oil to obtain treated kumquat oil.
After the treatment of Jin Jieyou, the pyrimethanil is reduced by 96.55%, the flavonoid compound is reduced by 58.62%, and the solubility in propylene glycol is improved from 0.1% to 0.25% compared with that before the treatment by GC-MS (gas chromatography-mass spectrometer).
Example 2
Mixing and stirring Jin Jieyou of a press and 1:1 of a 50wt% malic acid aqueous solution for 30min, refrigerating at-20 ℃ for 24h for layering, and separating upper essential oil to obtain the treated cumquat oil.
After the Jin Jieyou squeezing treatment is analyzed by GC-MS (gas chromatography-mass spectrometer), compared with the traditional method before the treatment, the pyrimethanil is reduced by 98.66%, the flavonoid compound is reduced by 53.70%, and the solubility in propylene glycol is improved from 0.1% to 0.3%.
Example 3
Mixing the squeezed sweet orange oil and 50wt% aqueous solution of tartaric acid at a mass ratio of 1:2, stirring for 35min, refrigerating at-15 deg.C for 20h for layering, and separating upper layer essential oil to obtain treated kumquat oil.
After the sweet orange oil is squeezed and treated, compared with the traditional method, the pyrimethanil is reduced by 97.56%, the flavonoid compound is reduced by 54.85% and the solubility in propylene glycol is improved from 0.27% to 0.45% through GC-MS (gas chromatography-mass spectrometer).
Example 4
Mixing the squeezed lemon oil and an oxalic acid aqueous solution with the mass ratio of 8.5wt% to 1.5, stirring for 40min, refrigerating at-10 ℃ for 16h for layering, and separating out upper essential oil to obtain the treated kumquat oil.
After the lemon oil is squeezed and treated, compared with the lemon oil before treatment, the pyrimethanil is reduced by 98.73 percent, the flavonoid compound is reduced by 59.21 percent, and the solubility in propylene glycol is improved from 0.15 percent to 0.34 percent through GC-MS (gas chromatography-mass spectrometer).
Example 5
Mixing squeezed grapefruit oil and 50wt% citric acid aqueous solution in a mass ratio of 1:1, stirring for 45min, refrigerating at-5 deg.C for 12h for layering, and separating upper layer essential oil to obtain treated kumquat oil.
After the cumquat oil is treated, compared with the cumquat oil before the treatment, the pyrimethanil is reduced by 93.58 percent, the flavonoid compound is reduced by 50.29 percent, and the solubility in propylene glycol is improved from 0.1 percent to 0.3 percent through GC-MS (gas chromatography-mass spectrometer).
Example 6
Mixing squeezed bergamot oil and 60wt% citric acid aqueous solution at a mass ratio of 1.2.
After the citrus bergamia oil is squeezed and treated, the pyrimethanil is reduced by 96.86 percent, the flavonoid compound is reduced by 51.84 percent, and the solubility in propylene glycol is improved from 0.1 percent to 0.26 percent by GC-MS (gas chromatography-mass spectrometer) analysis compared with that before the treatment.
Example 7
Mixing and stirring the squeezed bitter orange oil and an organic acid solution for 55min according to a mass ratio of 1.6; wherein the organic acid solution is formed by mixing 50wt% citric acid solution and 55wt% malic acid solution according to the mass ratio of 1:1.
By GC-MS (gas chromatography-mass spectrometer) analysis, the pyrimethanil is reduced by 98.84%, the flavonoid compound is reduced by 56.77%, and the solubility in propylene glycol is improved from 0.1% to 0.26% after the orange oil is squeezed and treated compared with that before the treatment.
Example 8
Mixing and stirring the pressed orange oil and an organic acid solution according to a mass ratio of 1.8 to 1.8 for 60min, then refrigerating at-8 ℃ for 18h for layering, and separating out upper-layer essential oil to obtain treated kumquat oil; wherein the organic acid solution is prepared by mixing a citric acid solution with the concentration of 40wt%, a malic acid solution with the concentration of 55wt% and an oxalic acid solution with the concentration of 8.0wt% in a mass ratio of 1.
After the orange oil is processed by GC-MS (gas chromatography-mass spectrometer), compared with the orange oil processed before processing, the pyrimethanil is reduced by 98.53 percent, the flavonoid compound is reduced by 57.59 percent, and the solubility in propylene glycol is improved from 0.1 percent to 0.31 percent.
Performance testing
The aroma components before and after the treatment with press Jin Jieyou (example 1) were analyzed by GC-MS (gas chromatography-mass spectrometer), the method and results were as follows:
gas chromatography conditions: the sample injection amount is 1 mu L; the column used was HP-5MS (30 m.times.0.25 mm.times.0.25 μm); the temperature of a sample inlet is 250 ℃; the temperature raising procedure is that the initial temperature is 50 ℃, the temperature is kept for 1min, the temperature is raised to 150 ℃ at the speed of 2 ℃/min, then the temperature is raised to 250 ℃ at the speed of 40 ℃/min, and the temperature is kept for 10min; the flow rate of the carrier gas is 1.0mL/min; the split ratio is 40.
Mass spectrum conditions: electron impact ion source (EI); electron energy: 70eV; the ion source temperature is 250 ℃; the temperature of a four-level bar is 150 ℃; the mass scanning range is 33-450 Da; the scanning mode is full scanning; delaying the solvent for 0min; the characteristic ions of the target are used for comparison and characterization with a NIST & Wiley spectral library.
The analysis results of the aroma components are shown in the following table 1, and the chromatographic peaks of pyrimethanil and flavonoids compounds are shown in the figure 1.
TABLE 1 comparison of GC-MS analysis of the components before and after pressing Jin Jieyou
As can be seen from Table 1 and FIG. 1, the fragrance of pressed Jin Jieyou treated in example 1 was not significantly changed, wherein the residual pyrimethanil content was reduced from 0.087% to 0.003% by 96.55%; the total content of the flavonoid compounds is reduced from 0.29 percent to 0.12 percent and is reduced by 58.62 percent. The processing method for the pressed citrus oil provided by the invention is shown to effectively reduce the contents of pesticide residues and flavonoid compounds, and improve the stability and safety of essential oil products while retaining aroma components.
The above is only a preferred embodiment of the present invention, and it is not intended to limit the scope of the invention, and various modifications and changes will occur to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention shall be included in the scope of the present invention.
Claims (6)
1. A processing method of pressed citrus essential oil is characterized by comprising the following steps:
mixing and stirring the squeezed citrus essential oil and an extracting agent, freezing and standing to separate the citrus essential oil into layers, and separating out upper-layer essential oil to obtain treated citrus essential oil;
wherein the extracting agent is an organic acid solution with the pH value less than or equal to 2.
2. A method of treating pressed citrus essential oil according to claim 1, wherein the organic acid comprises at least one of citric acid, tartaric acid, malic acid, and oxalic acid.
3. A method of treating pressed citrus essential oil according to claim 1, wherein the mass ratio of pressed citrus essential oil to extractant is 1:1 to 1:2.
4. The method of processing pressed citrus essential oil according to claim 1, wherein the stirring time for stirring is 30 to 60min.
5. The method of processing pressed citrus essential oil according to claim 1, wherein the freezing temperature of the freezing is-20 to 0 ℃ and the freezing time is 12 to 24 hours.
6. A method of treating expressed citrus essential oil according to claim 1, wherein the expressed citrus essential oil comprises at least one of sweet orange oil, lemon oil, grapefruit oil, bergamot oil, bitter orange oil, tangerine oil, and kumquat oil.
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| CN202210527330.0A CN115161112A (en) | 2022-05-16 | 2022-05-16 | Processing method of squeezed citrus essential oil |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009051738A (en) * | 2007-08-23 | 2009-03-12 | Yasuhara Chemical Co Ltd | Method for producing polymethoxyflavones, polymethoxyflavones produced thereby and aqueous solution of organic acid containing polymethoxyflavones |
| CN101415340A (en) * | 2006-04-07 | 2009-04-22 | 可口可乐公司 | Methods for removing contaminants from essential oils |
| CN101485311A (en) * | 2009-03-02 | 2009-07-22 | 深圳诺普信农化股份有限公司 | Aqueous solution of pyrimethanil |
| TW201026844A (en) * | 2008-11-11 | 2010-07-16 | Takasago Perfumery Co Ltd | Process for producing purified essential oil |
| JP2010235832A (en) * | 2009-03-31 | 2010-10-21 | Inoue Seikoen:Kk | Method for removing oil from pericarp of citrus fruit, method for powdering the pericarp of citrus fruit, bath agent and functional food composed of the powder, and method for producing powdery combined product from the pericarp of citrus fruit |
| CN106350228A (en) * | 2016-10-12 | 2017-01-25 | 广东李金柚农业科技有限公司 | Method for efficiently lowering agricultural residue content in essential oil |
-
2022
- 2022-05-16 CN CN202210527330.0A patent/CN115161112A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101415340A (en) * | 2006-04-07 | 2009-04-22 | 可口可乐公司 | Methods for removing contaminants from essential oils |
| JP2009051738A (en) * | 2007-08-23 | 2009-03-12 | Yasuhara Chemical Co Ltd | Method for producing polymethoxyflavones, polymethoxyflavones produced thereby and aqueous solution of organic acid containing polymethoxyflavones |
| TW201026844A (en) * | 2008-11-11 | 2010-07-16 | Takasago Perfumery Co Ltd | Process for producing purified essential oil |
| CN101485311A (en) * | 2009-03-02 | 2009-07-22 | 深圳诺普信农化股份有限公司 | Aqueous solution of pyrimethanil |
| JP2010235832A (en) * | 2009-03-31 | 2010-10-21 | Inoue Seikoen:Kk | Method for removing oil from pericarp of citrus fruit, method for powdering the pericarp of citrus fruit, bath agent and functional food composed of the powder, and method for producing powdery combined product from the pericarp of citrus fruit |
| CN106350228A (en) * | 2016-10-12 | 2017-01-25 | 广东李金柚农业科技有限公司 | Method for efficiently lowering agricultural residue content in essential oil |
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